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Home Contractor Evolution

Contractor Evolution | How to Implement a CRM Without Giving Yourself a Migraine

If you took a survey of contractors right after the implementation of their first CRM or Project Management tool, many of the responses you’d get would sound something like:

  • That was awful
  • My head nearly exploded
  • Truly the worst 6 months of my life for me and my team
  • I never want to go through that again

Technology and software are supposed to make your business life simpler and more efficient.  So why do most entrepreneurs talk about the adoption period like veterans talk about the war or mothers talk about childbirth?  

This whole “tech overwhelm” thing, especially for contractors, is something we’ve been wanting to get some answers on for a while now, which is why we are so excited to have Ben Hodson on the show today.  Ben is the Co-Founder and CEO of JobNimbus which is one of our favorite pieces of contractor software, and we thought who would be better to teach us how to implement technology headache-free, than the guy who builds it.  

We’re fans of Ben and JobNimbus for a couple of reasons. It's super customizable and integrates easily with everything. It's relatively simple to implement compared to other CRM’s and they have a dynamite customer support team that is super hands on. 

So if you’ve purchased a CRM and barely used it, if you’ve been frustrated by your tech stack or lack thereof, or if you’re still managing your business on a spreadsheet but you’re ready to take the leap… this episode is a must listen.

By the end of this episode you’ll know:

  • The difference between contractors that struggle to implement new systems vs those that find it pretty easy
  • How to use an “I.C.E.” decision making matrix to ensure you select the right CRM to begin with
  • How to avoid the common “employee pushback” scenario and foster adoption of any new tech system
  • How to identify all of the problems you face in business as one of two factors which then become easier to solve
  • The elements of the trades and contracting sectors are ripe for disruption and what you need to be getting ready for
  • The things that a serial CEO Ben Hodson wished he had learned earlier when running businesses


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Episodes

Episode 291    

If you’ve spent any time playing around with Claude, ChatGPT, Gemini etc., you’ve probably noticed how easy it is to put a ton of work into something that ended up being inaccurate, too complicated or more work than it’s worth. Tyler Folkman has worked in AI for almost 20 years, and in this podcast episode, he shares the roadmap for using AI in ways that actually benefit our business, our people, and our bottom line.

Contractor Evolution | What Happens When You Sell To Private Equity?

Episode 290    

There's a lot of noise about selling to private equity in the trades right now. If you’ve considered making it your exit strategy, there’s a few things you should know about the process. Today, private equity insider Tyler Goodhue is on the show to walk us through what actually happens when you decide to sell to private equity. The good, the bad and the ugly.

Contractor Evolution | The REAL Impact Of AI in Construction (And How To Prepare)

Episode 288    

When ChatGPT released in 2022, we all knew the start of a new era in tech was coming. But we couldn't possibly comprehend just how much our industry was about to change. Today, I've brought on DJ Carroll to talk about where the industry is now, where it's headed, and what we HAVE to learn to survive what he calls the next industrial revolution.

Contractor Evolution | : $7M Playbook: Build A Profitable Landscaping Company

Episode 286    

At just 30 years old, Riley Rivers owns a $7M landscaping business, pulling in $120K in profit every month. And he does it while working less than 40 hours a week. In this episode, he reveals the systems and people he put in place to make it happen.

Contractor Evolution | The Formula For Consistent Cash Flow In 7-Figure Contracting Businesses

Episode 285    

Ever run out of money despite making millions of dollars? This is the situation Bob Gauvreau has seen hundreds of contractors fall into. Revenue is up, profit may even be up. But they run out of cash unexpectedly and when they get hit with an unexpected bill or expense… …they crumple. In today’s episode, Bob walks us through a foolproof system for managing your cash flow so financial stress becomes a thing of the past.

Contractor Evolution | How Hiring ONE PERSON Doubled This Contractor's Business

Episode 284    

Alabama builder Joel Retherford finished 2025 at just under 3 million. By May 2026, he was already at 2.4. The only reason he was able to do this was by hiring a rock solid project manager. In this episode, he’s walking us through the process he used to recruit this critical hire, and how this one role is scaling his business while getting him out of the day to day.

Contractor Evolution | How This Contractor Made $200K From Change Orders

Episode 283    

Does your team see change orders as a necessary evil or an opportunity for profit? Texas builder Eric Olson used to make 2% on a year’s worth of change orders, largely because his project managers weren’t trained or incentivized to ensure they were in the company’s best interest before moving forward. After putting a system in place and aligning his team around it, Eric made 20% profit on change orders the next year. A 10X increase that came from an intentional focus on a “problem area” of the business.

Contractor Evolution | She Sold 600 Homes In A Year. Here's How $100M Contractors Scale.

Episode 282    

Most contractors struggle to close a million in sales. Today’s guest, Charlene Barrett used to sell hundreds of millions every single year. In this episode, she’s revealing the secrets to scaling operations without losing the quality of your work and customer experience.

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